


If The Shoe Fits

by mellowmallow



Category: Supernatural
Genre: Alternate Universe - Cinderella, Alternate Universe - Human, F/F, F/M, Fluff with a tiny bit of angst because drama, Heir!Dean, M/M, Waiter!Cas
Language: English
Status: In-Progress
Published: 2014-12-01
Updated: 2014-12-01
Packaged: 2018-02-26 07:37:19
Rating: Teen And Up Audiences
Warnings: Creator Chose Not To Use Archive Warnings, No Archive Warnings Apply
Chapters: 2
Words: 4,235
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/2643575
Author URL: https://archiveofourown.org/users/mellowmallow/pseuds/mellowmallow
Summary: <blockquote class="userstuff">
              <p>In which twenty-six year old Castiel Novak still thinks that a diary is the safest place to write his secrets and Dean Winchester has no respect for his roommate's privacy.</p>
            </blockquote>





	1. Blue

**Summary for the Chapter:**

> Boy meets boy.

_"Dean Winchester, hair of Winchester Motors reported missing. The twenty-five year old son of business owner John Winche---"_

 

Dean turns off the television.

 

Great. Just great. He's not exactly missing. More like "run-away son". It has been less than a week since his last argument with his father and one thing led to another. He left home soon after, grabbing a handful of clothes and shoving them into his duffel bag. He had also pulled out a thick wad of bills from his drawers because he refused to use the credit card his dad had gotten him on his eighteenth birthday (also because he would have been so easy to track then). With only a thin flannel over his favorite AC/DC shirt and a duffle bag of unimportant stuff, Dean hopped on the first bus out of Lawrence.

 

That was over three weeks ago.

 

Dean's been eating at cheap diners (which serve surprisingly good burgers) and living in cheap motels to lay low. He used to do odd jobs under odd names to earn his own keep, but he finally found his place (or at least, he likes to think he has) keeping inventory of candy in Singer's Sweets. He's living his own life for once, and despite the lack of the luxuries he's been used to having his whole life, Dean's never felt happier.

All good things come to an end though when his money runs out, and odd jobs can't pay for both good food and shelter. Cheap as motels go, it's still more expensive than living in an apartment; Which was what Dean should've bought when he had the cash.

 

After a two more days of unfruitful house hunting, he decides to phone his little brother Sam, who he hopes won't tattle his location to their dad (seeing their now mutual dislike for the man).

 

_"Hello?"_

 

"Hey Sammy. Long time no talk," Dean grins into the reciever. A wave of warmth floods over him. As much as he's enjoying life on his own, he misses his family, particulalry his little-big (or is it big-little?) brother Sam.

 

_"Dean?! Holy crap Dean! Where are you? Are you alright? You are alright, right? Otherwise you wouldn't be calling with that cheeky tone of yours. I saw the news! What happened? Dude this is great! I'm glad you're okay! I gotta tell mom and dad about this! Hold on for a sec, let me just---"_

 

"Woah, woah, wait Sammy don't!" Dean interrupts. "Just... calm down for a sec. Don't go telling anyone anything... uh, yet."

 

_"What? Why? Are you in trouble? Were you drunk driving? But that couldn't be the case, right? Because the only car you'd ever drive is your Baby, which Dad says is still in the garage, and you'd never drink and drive because the Impala's like your most precious possession so you wouldn't dare scratch it and---"_

 

"Sam---"

 

_"---or if you were caught dealing with drugs then the police should have caught you, I mean, you don't exactly keep a low profile Dean. Speaking of profile, the picture in the news is ridiculous. Couldn't Dad have found some normal picture of you? I mean, your hair is ridiculous. I can't believe you dyed it green! What are you? Thirteen and stuck in the middle of some identity crisis? Jeez, Dean. When will you learn to--- "_

 

"Sammy!"

 

_"---and another thing, why can't you just trust us for once? We can help you, Dean. I know you don't like asking for help with all your stupid masculine macho thing but you just have to learn to trust people! We're your family for Chuck's sake. Oh, by the way, Chuck's this really cool guy in my firm and there's this joke where---"_

 

"SAMUEL WINCHESTER!"

 

_"What? Why are you yelling, Dean? Jeez, now you have temper issues too!"_

 

  
"Do you have a big case coming up or something? Because it seems to be you've been drinking ten gallons of coffee,"

 

_"Yes, ugh, and I have to visit Adrianne tomorrrow too, not that I don't like visiting her---"_

 

"Woah, hold on there little brother. Do my ears decieve me? You're two-timing Jess?"

 

"Dude, Adrianne's Jessica's mother."

 

_"You're two-timing Jess with her mom? That's sick bro, even for you."_

 

_"What? No! I'm--- It's a friendly visit! And what do you mean that's sick even for me? Dean---"_

 

"Alright, alright. I'm just pulling your leg," Dean snickers into the phone. "Caffeinated you is easier to rile up than smartass-lawyer you. Anyway, I'm running out of minutes so let me cut this short. No, I'm not in any trouble. Not the legal kind anyway. Just with Dad. Dude wants me to get married to that bratty stuck-up Bela Talbot. So I ditched the engagement party and well, here we are a few weeks later."

 

_"Dean! Seriously? What are you, twelve? Woah wait, you and dad fought? Like, you disagreed with him on something?" Sam's voice sounds happy._

 

Figures. Sam and John had been decking out for years, disagreeing about everything.

 

Every fucking goddamned thing.

 

"Dude, I just told you. Jeez, you should stop drinking caffeinated drinks. They make you slower," Dean says.

 

_"Man, that's awesome! Finally!" Sam replies, ignoring his later comments._

 

Dean runs a hand through his hair and sighs. "Like I said, running out of minutes. And cash. And it pains me to say this but... I need your help, Samsquatch. I'm in this place called Sioux Falls."

 

_"Really? Wow, okay great! Adrianne lives there. So did Jess actually. I mean she lives with me now but... Anyway, I'll be there first thing in the morning."_

 

"Ugh, why are you such a morning person? Just don't go telling anyone we talked, okay?"

 

_"Even mom?"_

 

Dean stiffens a bit. He didn't mean to drag his mom into this. Mary Campbell Winchester is the nicest, most wonderful human being in the history of the universe. He feels bad for making her feel bad, but he needs this. "Yeah... Even mom. Just comfort her or something. But right now, I'd really like to be left alone."

 

_"Fine. But you owe me one hell of an explanation, Dean."_

 

"We'll talk when you get here," Dean nods solemnly. Not that Sam would see him nodding or anything.

 

_"Where are you staying?"_

 

"Aw, you're smart, Sammy! You'll know where to find me," Dean teases. It's not like there are a lot of motels in Sioux Falls anyway.

 

_"Oh come on, Dean---!"_

 

Dean snaps his phone shut and dives toward the unmade bed of the dingy motel room, burying himself in the deep azure blankets and dozing off while scrolling through John's angry texts and Mary's worried ones.

 

He dreams of blue.

 

* * *

Sam manages to find his brother approximately ten minutes after he hits town--- in the first motel he sees. It's not like Dean would have any reason to hide from him. And the fact that Dean expects him to be able to find his brother without so much a clue as to where he is is a clue in itself pointing towards where he is.

 

"Holy--- Wow, Dean. You kinda reek. No, scratch that. God, you smell terrible. How are you going to work like that anyway? How long has it been since you changed your clothes? Do you not know how to do your own laundry or something?" Sam complains loudly, wrinkling his nose at the smell. He held up a bag which Dean hopes contains fresh clothes and maybe some soap.

 

"Shut up, Sammy. It was just one day okay? I told my boss I was sick and couldn't make it so I didn't have to go to work smelling like horse shit," Dean scoffs and grabs the bag from Sam. He walks into the bathroom for a nice, long shower.

 

"So. Bela, huh?" Sam prompts.

 

"Can't this wait until after I shower?" Dean groans.

 

"Pretty sure you can shower and talk."

 

"And get soap in my mouth, sure."

 

"Then don't get soap in your mouth, stupid."

 

"I told him I'm into dudes and he totally flipped. Well not immediately." Dean pauses, remembering the way John had taken the news with a calm shrug and a short "okay, whatever makes you happy" speech. The next morning, he told me to suit up because I'm going to attend my engagement party at lunch and that's that. So I ditched."

 

"What did mom say? She wouldn't agree to that, you know she wouldn't."

 

"I didn't stick around long enough to find out," Dean admitted, wishing he had. Maybe things would have turned out differently. But then again, past weeks have been liberating, so he's fifty-fifty about it.

 

"You--- Ugh. I wish you'd be a little more patient, Dean. Mom was worried sick about you. She kept calling me every day to remind me tell her when I find you. Like she knew you'd contact me."

 

"Mom's psychic, that's what she is. Just... tell her not to worry. But don't tell her you've found me yet."

 

"Why not Dean? I'm sure she won't mind. She just needs to know you're still alive," Sam tries arguing, lawyer that he is.

 

"Yeah, and Dad'd see the difference in her behaviour and you know how Mom always tells Dad everything. Everything, Sam."

 

"Fine. Fine, but you better sort this out quick, not that there's even anything to be sorted out."

 

"Yeah? How's dad?" Dean asks, turning the shower knob off.

 

"Fuming."

 

"Exactly."

 

"Dean..."

 

"I mean exactly that. Dad's pissed I don't want to tie the knot yet. Probably ever," Dean shrugs. Sam sighs and shakes his head, probably about to start some speech on true love but deciding not to, knowing Dean probably wouldn't be listening to him anyway. Good choice, Sammy. 

 

"So... How long are you planning on staying away? You can't hide forever."

 

"I don't plan on hiding forever. Just a few weeks, maybe a year tops," Dean puts on his clothes and steps out of the bathroom.

 

"A year, Dean?! Are you insane? You couldn't even survive a week alone," Sam points out.

 

"No shit, Sherlock. I wouldn't have called you if I thought I could handle this alone."

 

"Since when do you ask for help?" Dean could see Sam's lips quirk upward and he knew his brother was enjoying this conversation.

 

"Since the day I realized how douchey of a dad Dad is to us. The enemy of my enemy and all that shit."

 

"Right," Sam grins, but doesn't say anything else. "So what exactly do you need my help for?"

 

"Well you mentioned you were familiar with this place. Thought you might know where I might find a cheap place to stay?"

 

"I could ask Adrianne if there's space in her apartment. I mean not her apartment per say; she's the landlady. I'm just not sure if she has vacant rooms."

 

"I'll take what I can get," Dean shrugs.

 

"Right uh... wait, let me just---" Sam takes out his phone and dials someone.

 

Dean grabs a razor from the bedside drawer and goes back into the bathroom to shave. He has a freaking peach fuzz now. He could hear Sam talking over the phone.

"Hello? Adrianne? Yeah, it's me Sam. Yeah--- Yeah, I'm fine, thanks. You? Good--- That's great. So, um... I just wanted to know if you have any more vacant rooms at--- No, no, no, it's not for me. It's for uh---

 

"Friend. Tell her I'm your friend," Dean mouths.

 

"She knows who you are, Dean," Sam replies in a whisper.

 

"Why did you tell her then?" But Sam ignores him.

 

"It's for Dean. Yeah, he's--- Wait, no, he's fine. He's not really missing just uh... wanted some uh... privacy. Dad's been working him real hard so he sort of... ran away. And Dad's pissed so... No, don't call them, please---

 

Dean's eyes grew wide at that. Shit, if Adrianne calls his parents then... Then... Then what? Shit, he doesn't even have a plan for that yet! Shit. Shit. Shit. Shit. Shit...

 

"Yeah, yes I know she's worried but... Adrianne please, it's kinda personal. You know how Dad is--- Yeah, okay. I will. Yes Thank you! Anyway, do you have a spare room? Oh. Well, sure, I'm sure he won't mind. Yeah, okay. Alright, thanks Adrianne. Bye."

 

"Did you have to reveal my whole back story?" Dean frowns.

 

"I couldn't lie to my girlfriend's mom," his brother shrugs.

 

"Come on. Bros before hoes man."

 

"Exactly," Sam smiles smugly.

 

"Bitch."

 

"Jerk."

 

"So? What did she say?

 

"She says she has one tenant who rents a three bedroom unit and if you don't mind sharing, which I told her you wouldn't, then she'd ask said tenant if he's okay with having a roommate. She'll call back tomorrow," Sam tells him.

 

"So I'm getting a roommate, huh? What is this, college all over again?" Dean grins, remembering Benny. If his roommate's half as awesome as he is, then he's sure they'd get along just fine.

 

* * *

 

The next day went by slowly, and Dean only received a text from Sam after his shift had ended stating the apartment's address. Which, hopefully means that he has a new home to look forward to living in. He'd already packed all his things back into his duffle which is sitting inside a locker in the employee's room at the back of the shop. After he locks up, he walks nervously towards the address, which is just three blocks from Singer's Sweets.

The place looks all bright and sunshiny even in the dim light of street lamps and windows. The walls were painted yellow and the window sills were mostly decorated with creeping vines and potted plants. Somehow, the place reminds him of Mary and her love for plants. Suddenly Dean misses her, and he quickly steps forward to knock before he loses his nerve and does something he regrets (like turn around and go home). He only has to knock twice at the mahogany door before a plump, middle-aged woman answers the door.

 

"You must be Dean. My, you have Sammy's eyes! Or, I suppose you both have your mother's eyes. Or father's. I wouldn't know, haven't met the happy couple yet! Oh, I've heard so much about you from Sam. Don't worry about your little problem. I won't tell a soul," she gushes and pulls him inside.

 

"Er... Thanks uh... Mrs. Moore," Dean responds uncertainly, looking around. The interior has a nice and cozy feel to it, with the plush but worn carpet and the fading, floral wallpaper that somehow is able to retain its charm throughout the years. It reminds Dean of simpler times, when his Dad wasn't such a workaholic and life was... good.

 

"Please, call me Adrianne," she smiles at him warmly. "And there's no need to thank me. If Sam's telling the truth, which I'm sure he is, then it's you I have to thank for raising such a great brother. He's been so good to my darling Jessica. A mother couldn't ask for a better boyfriend for her daughter."

 

"Oh. I don't--- um... I---"

 

"Oh just say thanks dear."

 

"Th-thanks," Dean looks down, cheeks hot.

 

"Now if you'll follow me, you're in room 109, that's this way, with Castiel Novak. He's a very sweet boy, so I'm sure you'll get along quite well. I'll be collecting the rent at the thirtieth of each month. Here's your key, dear. I hope you enjoy your stay," Adrianne puts the key in his hand.

 

"Thanks Mrs--- um, Adrianne," Dean says softly, eyeing the key on his palm.

 

"You're welcome, dear. And I know it's not my place to say, but do give your mother a call soon. As a mother myself, I daresay I know how she must be feeling right now."

 

"Alright, I have an important meeting to attend to, and I'm running a little late, so I'm going to have to apologize for leaving you to introduce yourself to Castiel. Oh but don't worry, he's a very nice boy and I've already informed him of your arrival so he should be expecting you. Have a good evening, Dean," she winks at him and leaves him in front of a white wooden door with the numbers 1-0-9 elegantly written on it in blue and silver paint.

 

"Yeah, you too," Dean mumbles and unlocks the door. Were it someone else in the room, he would have noticed how messy the place is, with paint splattered in most places. Dean stares at the man in the room, disheveled sex hair and baby blue eyes that he swears he has seen somewhere before, wearing a loose shirt and loose sweat pants that show off a peek of skin. He--- Castiel was staring back, probably just as surprised as Dean is, holding up a stack of papers in his arms.

 

Dean tries to shift his thought elsewhere. The guy was cute, he gives him that, but there is just no way he's about to make things awkward by flirting with his otherwise probably straight flatmate.

 

"So, Castiel right? Adrianne, the uh, landlady told me. I'm Dean," He offers his hand, trying to be as casual as possible." Nice to meet you."

  
Castiel stares at him for a long time before balancing the stack of papers on one arm and hesitantly shaking his hand. After a long moment of awkward silence, Dean pulls away while Castiel clears his throat and looks right into his eyes.

 

"Hello, Dean."

**Notes for the Chapter:**

> so this is gonna be an alternating chapter thing, where the odd-numbered chapters would be in Castiel's pov and the even-numbered ones would be Dean's, and Cas's would be in a diary entry format and Dean's would be in narrative form.
> 
> and idk, if there's any mistake in my grammar, but please point it out if there is. english isn't my first language, and if you want to beta for me then that'd be super amazing thanks <3


	2. Once Upon A Diary

**Summary for the Chapter:**

> Cas' point of view

_May 26, 2014_

_Michael insisted I keep a journal to track my thoughts. Said it'd help keep me company. Gabriel laughed at the idea and called it girly. Lucifer bought me a blank Moleskine. I don't understand why Michael wanted me to keep one, but I suppose there's no harm. It does feel like I have someone to converse to, even when I'm not talking per-say. Tonight's my first night alone in my new apartment. It feels odd not having Gabriel tearing through my door every five minutes to ask where Father kept the cookies._

 

_May 27, 2014_

_Michael dislikes my new job. He said that the service industry are for the poor, uneducated barbarians, as he so eloquently put. I quite like my new job though. It pays well, and I get to draw all sorts of interesting people in my spare time. Of course, that also means having to wait on insufferable individuals, but a lifetime of suffering being Gabriel's brother was not for naught. There are also two new tennants in the room across mine. They seem nice._

_Update: They are not nice. My new neighbors, Meg and Ruby Masters along with their mother Lilith are quite the miserly trio. They call me Clarence for some odd reason. Also I have been somewhat conned into doing their chores for them. Hannah tells me I'm too nice. Anna says I'm a pushover. I don't think I should seek my brother's counsel for this particular problem._

 

_May 29, 2014_

_I think I made a new friend. Or acquaintance. Pamela Barnes seems like a nice girl. She's friendly and popular among customers and staff. She's also creepy psychic. She told me we'd be a really great couple if not for the face that I like guys. I don't even know what gave it away. It's like she just peered into my mind. I'm sure my siblings (sans Michael) would love her though._

 

_June 4, 2014_

_Been a week. Too tired. Now I have both day and night jobs, thanks to the Masters. Meg somehow knows how to pick locks and the three of them often come over for breakfast. And by breakfast, I mean breakfast for them and scraps of leftovers for me. I'd consider moving out but there's this man at work I can't keep my eyes off. He has the greenest eyes. Michael would scold me for being so shallow, but he's the only reason why I even bother staying here and putting up with my neighbours's crap._

 

 

_June 8, 2014_

_His name is Dean (or at least, that's what Pamela said). He has really nice freckles. He's also a nice person who tips really well._

 

_June 9, 2014_

_Dean is probably straight. Somehow I wish he wasn't._

 

_June 10, 2014_

_I'm pinning over a man who does not even know of my existence. I can already imagine Lucifer and Gabriel's mocking tones._

 

 

_June 11, 2014_

_He smiled today. Not at me, but I wish I had taken a picture anyway. I don't think my sketch can capture the beauty of his smile. This Moleskine is beginning to resemble that of a hormonal teenage girl's. I only pray that no one reads this, ever. I'm gonna have this journal burn with me when I die. I swear it on my mother's grave._

 

 

_June 12, 2014_

_Dean didn't come today. Nothing new, I suppose. It's not like he has to be at the restaurant everyday. I just wish he were._

 

_June 13, 2014_

_No Dean today. Green reminds me of him now. I called Hannah about it. She laughed at me and told me I'd get over it or it'd get over me. I'm not sure how to reply to that. Anna was even less of a help, and god forbid I ask my brothers. I hate how the pages are starting to be filled with Dean._

 

_June 14, 2014_

_Michael called. Said he got engaged and thought I'd like to know. I can't believe he's getting engaged. Since when did Michael have a girlfriend? I've only been gone less than a month. Hannah tells me he's had a girlfriend for years. How can I not notice that, seriously._

 

_June 15, 2014_

_I hate my job. Some customer thinks because I'm "just a waiter" means he can get away with disrespect. Here's a sketch of said customer. I abhor him with a burning passion of a million suns._

 

_June 16, 2014_

_I have accepted the fact that Dean had probably either grown tired of our food, moved out of town, or found out about my disturbing, secret admiration for him. Doesn't mean I need to stop sketching him._

 

_June 17, 2014_

_Day off, gone to the library to find the tallest man I've ever seen in my life, and quite possibly the most polite one too. We talked about various subjects from classic literature to human rights and respect. He was an interesting man, but his eyes keep reminding me of Dean. They're almost the same shade, only Dean's are a little brighter. Like the way the sun shines on the grass to make it just a little brighter than usual. I tell Hannah this. She tells me to get laid._

 

_June 18, 2014_

_It's raining really hard tonight. Weather man says a storm's coming. No shit Sherlock. I toast smores on my stove. They remind me of Dean's hair. He has toasted marshmallow hair. I'm willing to bet it feels just as soft. I'm forgetting what he looks like. My sketches are slowly becoming the only memory of his features._

 

_June 19, 2014_

_How do you not get over someone you barely even know?_

 

_June 20, 2014_

_Sometimes I wonder why the Masters don't just hire a housekeeper. I dislike having to do all their chores, yet I find myself doing them anyway. I should probably stop._

 

_June 24, 2014_

_I told the Meg to do her own laundry when she shoved her basket at me after breakfast today. She seemed impress that I was finally "growing a pair". I thought she'd yell or scream or something. Ruby only rolled her eyes and Lilith announced loudly that she still wouldn't be doing her own. Meg's actually surprisingly fun to draw. Her facial expressions are amusing._

 

_June 26, 2014_

_Meg is quickly growing to be what seems to be my only friend in the city. You'd think a month would be more than enough time for me to go and socialize. I told her about Dean. She laughed at my misery and told me I was way in over my head falling for a Winchester. I've wasted a page trying to copy Dean's shade of green._

 

_June 27, 2014_

_Meg sometimes sleep over. She has also read my journal. She told me how boring my life was and that she'd spice it up for me. I have a feeling I'm going to regret ever welcoming her into my apartment. Speaking of welcoming people to my apartment, Mrs. Moore (the landlady) asked me if I didn't mind having a flatmate. I tell her I don't. I just hope it's not Gabriel._

 

_June 30, 2014_

_Saying yes to a new flatmate turned out to be either the best or worst decision of my life. Guess who._

_Dean. dean deaN deAN dEAN DEAN DEAN DEAN._

_I think I might just loose it. He's sleeping in the room next to mine. Or at least, I think he's sleeping. I hope he's sleeping. I called Hannah. She told me to "be myself and remember to use protection". Gee thanks Hannah, that helps a fuck ton. I still can't believe I'm sharing an apartment with a guy I've been pining for for weeks! Mrs. Moore says he'd only be here a few weeks, or maybe a couple of months. I don't know if that piece of information should make me feel better or worse. Somehow, sharing a room with Gabe doesn't seem so bad anymore._

**Notes for the Chapter:**

> *edited Dec 2, 2014*
> 
> basically, you'll see both Dean and Cas's point of view. Dean's is more broad and descriptive, while Castiel's is a more biased and summarized version of Dean's that comprises mostly of his thoughts.
> 
> Also while Dean's POV covers a few days, Castiel's will cover the whole month (or at least, most of it)
> 
> Sorry for the confusion!

**Author's Note:**

> Sort of a Cinderella story, idk. I just had this idea I wanted to write. :p  
> Also, there will be other pairings later so yeah.


End file.
